Ryan Sandler is the Co-Founder and CEO @ Truework, the company that gives employees control over employment, income and other identity data. To date, Ryan has raised over $44M with Truework from the likes of Sequoia, Khosla, Menlo and from the founders of companies such as Plaid, Seatgeek, Mino Games and Checkr. Prior to founding Truework, Ryan spent 3 years as a Senior Product Manager @ LinkedIn.

 In Today’s Episode We Discuss:

• How Ryan made his way from LinkedIn Product Manager to founding Sequoia backed Truework and changing the world of identity data?
• Why does Ryan believe it is such an advantage to sell into mid-market? Where do most people go wrong here? How can startups show credibility to mid-market when they are so small? How can founders use case studies and references to build social credibility early on?     
• What have Ryan’s lessons been when it comes to pricing? How does Ryan think about and approach discounting? How does Ryan feel about pilot plans? What elements can founders negotiate on to get the best pricing?    
• Why does Ryan believe SEO is the best-kept secret in SaaS? How has Ryan structured his content and marketing team as a result? How can one automate as much of the content creation process as possible? How long should one expect in terms of lead times to see returns on the SEO strategy?    

Ryan’s 60 Second SaaStr:

1. Hardest element of Ryan’s role with Truework?
2. What would Ryan most like to change about the world of SaaS?
3. What does Ryan know now that he wishes he had known at the beginning? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Ryan Sandler

From how many reps to hire, to compensation models, here are the top 10 mistakes founders make when hiring their first sales teams and how to avoid them. 

Investment can create more problems than it solves and founders may trick themselves into thinking they have product-market fit when they don't. Michael Seibel, CEO @ Y Combinator explores the top risks founders should be aware of after funding and his best tips to avoid them.

Dave McJannet is the CEO @ Hashicorp, one of the fastest-growing enterprise companies of our time providing consistent workflows to provision, secure, connect and run any infrastructure for any application. To date, the company has raised $349M in funding from some of the best in the business including Bessemer, Redpoint, True Ventures, IVP, Mayfield, TCV and GGV to name a few. As for David, prior to Hashicorp, he held some incredible roles including VP Marketing at Github and Hortonworks, Senior Director of Product Marketing @ VMWare and then also spent over 5 years at Microsoft. 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

In part two, ZoomInfo founder and CEO Henry Schuck shares how he built a business from scratch and grew it into one of the most successful IPOs of the 21st century—and what it was really like...the good, the bad, and most of all, the ugly. He reflects on where he went wrong, what he would do differently, and how to avoid making the same mistakes he did.

GitHub’s COO, Erica Brescia, shares her experiences and lessons learned from her former life on the front lines of being a co-founder of her own company, and how those lessons apply to her current position overseeing operations for GitHub. 

ZoomInfo founder and CEO Henry Schuck shares how he built a business from scratch and grew it into one of the most successful IPOs of the 21st century—and what it was really like...the good, the bad, and most of all, the ugly. He reflects on where he went wrong, what he would do differently, and how to avoid making the same mistakes he did.

Bessemer's 5th Annual State of the Cloud Report returns for a definitive look at the cloud industry today. Byron Deeter and Elliott Robinson, partners at Bessemer Venture Partners, offer macro trends in the public and private cloud markets, strategic advice to cloud founders, and insights into why entrepreneurs should feel auspicious about the future.

Latane Conant is the Chief Marketing Officer at 6Sense, the company that allows you to achieve predictable revenue growth by identifying accounts looking for your solution, prioritise efforts and then engage the right way. To date, the company has raised $120M in financing from Battery Ventures, Insight, Venrock, Costanoa, Bain Capital and Salesforce Ventures to name a few. As for Latane, before 6Sense she was CMO and sales leader at Appirio where she drove 5X more effective field marketing programs and an increase in inbound leads by 300%. If that was not enough, Latane is also on the Advisory Boards of both Mediafly and Atrium. 

 In Today’s Episode We Discuss:

• How did Latane make her way into the world of SaaS and come to be the rockstar CMO and ABM thought leader she is today with 6Sense?
• What does the preparation process look like pre-sales kick off week? What is involved? Who is involved? What needs to be ready? How does Latane feel about putting comp plans as part of the week?     
• How important is a theme to having an engaging week of content? What can teams do to bring their themes to life? How does Latane advise others when it comes to keeping the content fresh and exciting?  
• What is the right way to end the week? What are the right follow up steps to take? Where do many people go wrong here?    

Latane’s 60 Second SaaStr:

1. Hardest element of Latane’s role today with 6Sense?
2. What would Latane most like to change about the world of SaaS?
3. What does Latane believe that most around her disbelieve? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Latane Conant

It’s no secret that businesses today are struggling with an unpredictable economy. In this session, Mailchimp Co-founder and CEO Ben Chestnut will share the story of Mailchimp’s founding amidst—and despite—the dot-com bubble burst, and how the company navigated a number of inflection points in the first 10 years of its founding. 

As organizations race to achieve relevance and a competitive edge in the digital era, automation is fueling the fight. Join PagerDuty’s CEO, Jennifer Tejada, as she discusses the need for agility and innovation and how automation is aiding adaptability and allowing enterprises to surge ahead.

In today’s SaaStr Insider episode, SaaStr CEO and Founder Jason Lemkin and the Co-founder and CEO of HireSweet, Robin Choy, share their experiences building and scaling their companies.

Today's SaaStr insider originally aired on A-Players, a new podcast that teaches you how to hire, retain, and train top performers for your team! 

Success in the Enterprise means ensuring consumerization is a part of your strategy. Scott Belsky, CPO, EVP of Creative Cloud at Adobe will explore key tactics to focus on the user experience.

Hilary Headlee is Head of Global Sales Operations and Enablement @ Zoom. Prior to joining Zoom, Hilary was VP of Global Sales Operations and Productivity @ MindBody and before that enjoyed similar roles with Alteryx, Invoca and Lynda.com. At Lynda.com, Hilary grew the support teams from 6 to 60 people and supported more than 60 net new reps in just 3 years. If that was not enough, Hilary is also a Limited Partner in Stage 2 Capital, the venture firm focused purely on go-to-market. 

 In Today’s Episode We Discuss:

• How did Hilary make her way into the world of SaaS and come to be the sales leader she is today with the global communications leader, Zoom?
• When thinking about sales ops vs revenue ops, what are the 4 key points to consider for founders? How does lead management and onboarding alter the question of sales ops vs revenue ops? Where does Hilary see operational debt the most? How does she advise founders on removing it?    
• Given the broad scope of sales ops and engagement, is it not just rebalancing culture, comms and change? As a business scales does there not come a time where it unbundles and scales out of sales vs revenue ops? How do the roles change with time and scale? Where do the breakpoints occur? 
• Why does Hilary believe documentation is so important today? What is the toolset Hilary uses for documentation? How does Hilary train her team around the right strategy to document their processes? Where do many go wrong here? Where can you pick up small wins?   

Hilary’s 60 Second SaaStr:

1. What is the hardest element of Hilary’s role today with Zoom?
2. What would Hilary most like to change in the world of SaaS today? 
3. What does Hilary believe that most around him disbelieve? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

The buzz that accompanies digital transformation trends is infinite. Cut through the noise with Aaron Levie, CEO of Box and Jason Lemkin, CEO & Co-founder of SaaStr as they share insights on what will make a lasting impact and what may fail to materialize in the future of work.

Centralized HQs with all the perks and amenities “under one roof” have traditionally been used as recruiting tools to attract and retain top talent. In this episode, Justin and Jen discuss what the Office of the Future will be like. 

Kyle Parrish is the Head of Sales @ Figma, the company that helps teams create, test and ship better designs from start to finish. To date the company has raised over $132M in financing from some of the best in the business including Sequoia, a16z, Index, Greylock and Kleiner Perkins to name a few. As for Kyle, prior to Figma he spent over 5 years at Dropbox achieving some incredible milestones including launching and scaling the Austin, Texas office from 3 to 80 people and being responsible for growing Dropbox’s leading partner ecosystem. Before Figma, Kyle spent close to 3 years as an Account Executive at ADP. 

 In Today’s Episode We Discuss:

• How Kyle made his way into the world of SaaS and sales and came to be Head of Sales at one of the fastest-growing companies in Figma?
• Kyle was in charge of creating the Austin, Texas sales team @ Dropbox, what were some of his biggest lessons when it comes to moving sales outside of HQ? What worked? What did not work? At what stage does culture and process really start to break?    
• Why is it so hard moving from 0-1 in sales? How does Kyle advise founders when it comes to making your first sales hire? Does Kyle agree that it has to be the founder who develops the sales playbook? How does one create sales targets that are both ambitious but also achievable? What is the balance? 
• What does it take to create a performance led sales culture? Where do many people go wrong here? How is the best way for sales and product to work together? What can one do to proactively make those discussions with sales and product both frequent and productive?   

Kyle’s 60 Second SaaStr:

1. What is the hardest element of Kyle’s role today with Figma?
2. What would Kyle most like to change in the world of SaaS today? 
3. What does Kyle believe that most around him disbelieve? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Kyle Parrish

The future of work is here and digital automation is now essential for today’s workforce. Tools have improved, but companies are STILL using outdated and manual processes to conduct business. Enter Pipefy. Pipefy is a workflow management software that makes business processes such as purchasing, onboarding, and recruiting—hassle-free, so requesters, processors and managers are more efficient. Pipefy seamlessly integrates with other tools in your toolchain to ensure a completely automated experience with a low to no code implementation. Dispersed or remote team members? NO PROBLEM! Pipefy can automate your requests from anywhere. Scroll over to pipefy.com/saastr to try it out and get 10% off your first 3 months. Empower your teams everywhere with Pipefy.

Small, Medium, or Enterprise, SaaStr CEO Jason Lemkin sits down with Shopify Plus GM, Loren Padelford, to discuss how to keep your customers happy at all stages.

Customers' expectations are higher than ever with more access to information and options. This dynamic trio of SaaS experts share how to stay customer-centric and set yourself apart in today's rapidly changing environment.

Lara Caimi is the Chief Customer and Partner Officer @ ServiceNow, the company that allows you the power to make work, work better. Prior to their IPO, ServiceNow raised funding from some of the best in the business including Sequoia Capital and Greylock. As for Lara, she joined ServiceNow in 2017 and spent 3 years as Chief Strategy Officer before assuming her current role just this month. Before ServiceNow Lara spent an incredible 17 years at Bain & Co across a variety of different projects and roles.

 In Today’s Episode We Discuss:

• How Lara made her way into the world of ServiceNow and SaaS having spent an incredible 17 years at Bain & Co?
• What does the role of Chief Strategy Officer really entail? How did the role change in Lara’s 3 years in the position? What is the optimal relationship between the Chief Strategy Officer and the CEO? How does Lara advise founders on when to hire their Chief Customer Officer?  
• How does Lara see the 4 phases of startup growth? What are the most challenging elements within each? How does one instil process and discipline without losing agility and speed? How does one set targets that are a stretch but also not a stretch too far? What is the right balance? 
• How does Lara think about what great change management looks like today? How does that change in a COVID world? How does Lara approach the right way to address enterprise customer communications? Why has that been made easier in COVID times?  

Lara’s 60 Second SaaStr:

1. What would Lara most like to change in the world of SaaS today?
2. What is the hardest element of Lara’s role with ServiceNow today?
3. The biggest surprise for Lara internally since the start of COVID? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

The future of work is here and digital automation is now essential for today’s workforce. Tools have improved, but companies are STILL using outdated and manual processes to conduct business. Enter Pipefy. Pipefy is a workflow management software that makes business processes such as purchasing, onboarding, and recruiting—hassle-free, so requesters, processors and managers are more efficient. Pipefy seamlessly integrates with other tools in your toolchain to ensure a completely automated experience with a low to no code implementation. Dispersed or remote team members? NO PROBLEM! Pipefy can automate your requests from anywhere. Scroll over to pipefy.com/saastr to try it out and get 10% off your first 3 months. Empower your teams everywhere with Pipefy.

Digital transformation marks a radical rethinking of how companies use tech, people, and operations to fundamentally change their business performance. Coupa CEO, Rob Bernshteyn, and SaaStr CEO, Jason Lemkin, will discuss how the Cloud has changed in 2020.

From strategies in recruitment and team building to sales tactics, these leaders from Salesforce, nCino, and Vlocity, will discuss the top tips for moving beyond horizontal SaaS and building a billion-dollar SaaS company.

Chen Amit is the Founder & CEO @ Tipalti, the only global payable automation platform that scales with you and now remitting $5Bn annually across 3M suppliers. To date, Chen has raised over $146M with Tipalti from the likes of Oren Zeev, Dan Rose, Mike Chalfen and then Greenspring, Truebridge and 01 Advisors to name a few. Previously, Chen was CEO of Atrica, acquired by Nokia-Siemens. He also was co-founder and CEO of Verix. At ECI Telecom, Chen founded its ADSL business unit and led it from inception to $100 million in annual sales. 

 In Today’s Episode We Discuss:

• How Chen made his way into the world of SaaS and came to found the leader in account payables with Tipalti?
• Why does Chen believe so much of his success is derived from saying no to customers? How does Chen determine which customer feedback to ingest vs to reject? If rejected, how can startups do this in a polite and respectful way? How can startups give the appearance of a large company to enterprises?   
• Given the infinite supply of capital, how does Chen think about unit economics? How does Chen think the right way to calculate LTV is? Where do many go wrong? What can we learn from Amazon when it comes to LTV? How does Chen advise founders to think about annual dollar churn? 
• How does Chen think about optimising pricing models today? How can SaaS companies have variable pricing mechanisms without disincentivizing usage? How does Chen think about aligning revenue scale to your customers? How can this be done? What are the benefits?  

Chen’s 60 Second SaaStr:

1. What is the hardest element of Chen’s role today with Tipalti?
2. What would Chen most like to change in the world of SaaS today? 
3. What does Chen believe that most around him disbelieve? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

The future of work is here and digital automation is now essential for today’s workforce. Tools have improved, but companies are STILL using outdated and manual processes to conduct business. Enter Pipefy. Pipefy is a workflow management software that makes business processes such as purchasing, onboarding, and recruiting—hassle-free, so requesters, processors and managers are more efficient. Pipefy seamlessly integrates with other tools in your toolchain to ensure a completely automated experience with a low to no code implementation. Dispersed or remote team members? NO PROBLEM! Pipefy can automate your requests from anywhere. Scroll over to pipefy.com/saastr to try it out and get 10% off your first 3 months. Empower your teams everywhere with Pipefy.

Therese Tucker breaks through the dogma behind what it takes to build a successful tech company. With stories based on the founding of BlackLine — to the company’s successful IPO – you’ll learn the most common myths behind success and why they may be holding you back.

Pete Kazanjy is the Co-Founder @ Atrium, the startup providing proactive, always-on insights for sales operations, managers, and leaders. Stop asking questions. Start getting answers. Alongside Atrium, Pete is also the Founder of Modern Sales Pros, a community of 15,000 focused on sales operations and sales management. Pete is also the author of Founding Sales, the canonical writing on early-stage startup sales. Prior to founding Atrium, Pete founded TalentBin, culminating in their exit to Monster Worldwide in February 2014. Finally, before TalentBin, Pete founded Honestly.com building the world's first professional reputation clearinghouse and raising funding from CRV and First Round in the process. 

 In Today’s Episode We Discuss:

• How Pete made his way into the world of SaaS and how he came to be one of the leading figures on sales operations and management that he is today?
• Why do founders have to sell the product themselves at the start? When is the right time to hire their first sales reps? What profiles should founders look for in these first reps? What are the most common mistakes founders make when hiring their first reps? How should they structure their comp plans?   
• How do the best onboard their sales reps? What can be done to minimise ramp time of new reps? How is the documentation used most effectively? How can sales calls be used for new rep onboarding? How does Pete think about optimising payback period on a per rep basis? 
• What are the leading indicators that a sales rep is successful? What are the core metrics founders should measure to determine the effectiveness of their reps and sales teams? How does this differ between SMB and enterprise? What are the challenges with enterprise given the long sales cycles? 

Pete’s 60 Second SaaStr:

1. Hardest element of Pete’s role today with Atrium?
2. What would Pete most like to change in the world of SaaS?
3. What sales leader does Pete most respect and why?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Pete Kazanjy